56 Years Ago: Buddy Holly Killed In a Plane Crash

Fifty-six years ago as of yesterday (Feb. 3, 1959) was an incredibly tragic day for music fans. It was on this day thatÂ Buddy Holly was killed in an airplane crash, attributed to poor weather and pilot inexperience, near Mason City, Iowa. The Big Bopper and Ritchie Valens were also passengers on the private flight and died in the crash — and if it wasn’t for an act of kindness,Â Waylon Jennings would have been on the plane as well.

Holly first met Jennings when they were both aspiring artists in Lubbock, Texas. The future country legend worked at a local radio station and began playing Holly’s music after the two struck up a friendship. In turn, Holly took a keen interest in Jennings, helping him with his image and arranging recording sessions for him. He also hired Jennings to play bass for him on a three-week tour across the Midwest, dubbed the Winter Dance Party Tour, which also included Dion and the Belmonts, Valens and the Big Bopper.

Due to previous tour bus mechanical failures, Holly chartered a small airplane to get him from a Feb. 2 concert in Clear Lake, Iowa, to Fargo, N.D. Jennings had planned on accompanying Holly on the flight, but the Big Bopper had the flu, so Jennings gave him the seat on the ill-fated plane and took the bus instead.

When Holly learned that Jennings wasn’t planning on flying with him, so the story goes, he said to Jennings in jest, “Well, I hope your ol’ bus freezes up,” which prompted Jennings to joke, “Well, I hope your ol’ plane crashes” — a statement that Jennings admits haunted him.

“For years, I thought I caused [the crash],” JenningsÂ said years later. “Somebody had taken my place on that airplane. And then I had told Buddy, ‘I hope your plane crashes.’ We cut up like that all the time.”

In 1978, Jennings included the song ‘A Long Time Ago’ on his ‘I’ve Always Been Crazy’ album. The tune, written by Jennings and Shel Silverstein, alluded to the plane crash, which at that time had happened almost 20 years before, and Jennings’ dislike of discussing it.

“Don’t ask me who I gave my seat to on that plane,”Â Jennings sings in the song.Â “I think you already know / I told you that a long time ago.”

Holly was buried on Feb. 7, 1959, in Lubbock. Jennings continued performing with the Winter Dance Party Tour, which made him unable to attend the service. Holly was 22 years old at the time of his death.